Well worth the hour drive from St. Louis, this clockwise loop begins at a gravel parking lot and heads east for 100 yards before splitting to begin the loop. The recommended clockwise approach heads downhill and turns east through a set of slot canyons toward a forest of formations known as “Cauliflower Rocks,” and past a set of head-high arches. Sub-surface seeping and sheer cliffs combine to create cool, damp conditions that encourage ice-age like species of ferns and mosses on this trail, but also beautiful displays of spring flowers. About a half-mile in, a sturdy wooden bridge crosses Pickle Creek for the first time. The east end of the loop dips toward the 50-foot walls of Spirit Canyon at the half-way mark, but mostly traverses a forested trail sprinkled with a dusty layer of sand—it’s also flanked by poison ivy, so stick to the trail. Dome Rock and Owl’s Den Bluff overlook the forested valley to the west before the trail descends again to cross Pickle Creek near a delicately dripping fall. The observation platform at Headwall Falls is less than 0.25 mile from the trailhead and is a memorable stop before closing the loop. -Mapped by Bill Yearout

Stop for photo ops at climb-worthy Cauliflower Rocks and the shaded Double Arch just up ahead.

PKL006

Location: 37.802743, -90.297541

Near mile 0.6, the trail winds through boulders and tucks through "the Keyhole." Continue winding downhill to the creek crossing.

PKL007

Location: 37.8028754, -90.296663

There is a sturdy wooden bridge over Pickle Creek, enjoy listening to the water flow over the rocks before heading uphill. Though the sandy trail shows evidence of the areas geology, the next major formation is about 0.5 mile through the forest.

PKL008

Location: 37.8003916, -90.2928436

Large open cliffs precede the contour of Spirit Canyon at mile 1.1. From here, the trail climbs 100 feet toward a valley-view outcropping in 0.3 mile.

PKL009

Location: 37.801364, -90.295968

Dome Rock precedes Owl's Den Bluff, a great place to climb and admire views of the forested valley below. Watch children carefully and use caution around the steep and accessible edges of the rocky outcropping. The trail loops north, then around the bluff toward the spring below.

PKL010

Location: 37.801036, -90.297002

A bridge crosses Pickle Springs, the namesake feature of this 256-acre Natural Area that flows toward the Mississippi River.

PKL011

Location: 37.800132, -90.299215

A short, wooden boardwalk and observation platform offer up-close views of Headwall Falls. After a spring rain, water pours over the cliff into the gorge.

PKL012

Location: 37.801204, -90.300005

The understory opens as the trail cruises through Piney Glade just before the loop closes. Turn left to backtrack to the trailhead.

Trail Kiosk

Location: 37.8014597, -90.3007802

The large trail map near the trailhead also has a box of detailed hike guides which explains the formations en route.

Rocky Ledge

Location: 37.8017903, -90.3005254

This ledge alongside the trail near its start is a preview of the sandstone formations up ahead.

The Slot

Location: 37.8028945, -90.3008607

Looking down into the upper entrance of the sandstone "slot"

Erosion

Location: 37.8026444, -90.3005683

Beaches of a long-gone sea, the sandstone formations in, around and including the slot, have been carved by water and erosion over the eons. This cave inside the slot is one example.

Icicles

Location: 37.8024177, -90.2999783

Winters low temperatures and cool, damp temperatures turn water seeping through the sandstone into cliff-side icicles.

Cauliflower Rocks

Location: 37.802263, -90.2976286

Take some time to climb on and explore Cauliflower Rocks, from the top, there's a great view of the forest below.

Double Arch

Location: 37.8021909, -90.2974623

It's possible to walk through these arches as you continue on the trail toward Pickle Springs.

The Keyhole

Location: 37.802725, -90.2974865

Spirit Canyon

Location: 37.8003662, -90.2928758

The sandstone cliff faces of Spirit Canyon.

Owl's Den Bluff

Location: 37.8013919, -90.2957618

The rocky top of the bluff is just off of the main trail but offers expansive views of the valley.

Dome Rock

Location: 37.8011037, -90.2957618

Owl's Den Bluff

Location: 37.801358, -90.2967596

A view of the bluff from the valley floor. You might spot other hikers on top of the viewpoint you just left.